Osterville MA Homes for Sale

Find the latest homes for sale in Osterville, MA with Buyer Brokers of Cape Cod. Save your favorite listings to your account. If you don't have an account with us, you can register here. You'll be able to keep track of your saved listings and when new properties match your search criteria.

Be sure to contact us to schedule a showing for any listing below or if you have any questions about the Cape Cod real estate marker.

Overlooking the beautiful waters of East Bay and Nantucket Sound sits this sophisticated yet intimate waterfront estate. The current owners completely renovated the 11,578sf home from stem to stern with the highest grade materials and exceptional craftsmanship. Interior spaces are bathed in natural light with beautifully balanced living areas all oriented toward the water. You'll find a welcoming foyer with original wood floors, living and dining rooms with custom fireplaces, a spacious, well-equipped kitchen and a handsome library with hand pegged wood. Casual spaces for family and friends include a family room, sunroom and enclosed porch. The second level offers 2 master suites and 7 additional bedrooms. An expansive lawn, in-ground pool and scores of privacy trees dress the 5.46 acre site. A custom beach house enhances the private dock. The property offers a detached 5 car garage with a gorgeous 3 bedroom carriage house above for guests and extended family.

Exquisite waterfront estate located on one of Cape Cod's most coveted streets combines the best of elegance, style and craftsmanship. This one of a kind French Mediterranean inspired home, with 2.72 acres, offers an unparalleled 620 feet of white sandy beach anchored by two substantial, private deep-water docks and unobstructed water views. The timeless and enchanting 7,000+ sq.ft. home with 5 bedrooms features well-proportioned rooms with high ceilings, wide planked floors, arched doorways, a stunning new gourmet kitchen and master bedroom with new bath. Enjoy dining al fresco on tiered terraces surrounded by colorful gardens and witness the amazing sunsets overlooking the Seapuit River and West Bay. This breathtaking home, with a two-bedroom updated guest house, remains close in proximity to upscale boutique shopping and fine dining. This is a unique offering that will captivate the most discerning buyer. There really is no comparison!

Classic Cape Cod Estate! This stunning and traditional Royal Barry Wills waterfront residence sits on the banks of Cotuit Bay and offers magnificent water views, 275 feet of water frontage and inspirational sunsets. Capturing the luxurious spirit of Oyster Harbors, a private gated community, this home features elegant interiors with rich details, modern comforts and extraordinary views. Dramatic vaulted ceilings and expansive windows; sprawling master suite; chef's kitchen with two granite center islands; handsome home library; a fabulous entertainment room in the lower level; and formal and informal living spaces all provide ample room to host family and friends. The 1.52 acre site combines access to outdoor adventure and modern amenities in a natural setting. Add in a private 2 bedroom guest house, an in-ground pool, sandy beach and private dock, and this property takes your life to new heights!

Land's End, a classic Old World Estate situated on 4.15 acres where the waters and shores of Nantucket Sound meet Osterville's West Bay, is available for the first time in 100 years. Grand, yet unpretentious, the home provides three floors of gracious entertaining and living spaces for family and guests, and offers unsurpassed panoramic water views spanning Nantucket Sound and down the Seapuit River to the West. A classic beach cabana with an expansive deck overlooking the private 500+ feet of white sand beach, brings you back to an era of easy summer living. The boat house provides storage for numerous boats and allows for easy launching from the beach. A private tennis court adds to the resort lifestyle and fits nicely into the natural landscape of the estate. This is truly a once in a life time opportunity to capture this spectacular and rare location with frontage on both Nantucket Sound and West Bay, and create your own memories for generations. Buyers to verify all information.

461 Main Street is the epitome of luxury waterfront living on Cape Cod. This exquisite estate is situated in the heart of Osterville overlooking East Bay and Nantucket Sound offering stellar views. From the minute you enter the dramatic front door you are impressed by the quality and attention to detail throughout. From the furniture quality windows and doors, custom bronze railings, wenge inlaid oak paneling and custom cherry cabinets you know no expense was spared. All 5 bedrooms are en suite and there is an elevator for easy access. You will enjoy entertaining whether by the infinity pool/spa, in the billiards/game room, in the theater or launching a boat from your private dock. The private office on the third floor offers the best view on Cape Cod! A magical lifestyle!!

Fronting on West Bay and overlooking Oyster Harbors across the water, this 6 bedroom, Patrick Ahearn remodeled home offers the highest quality construction and modern home control technology. Deep water dock with small beach, tennis court, and professionally landscaped grounds are only a few of the special features of this spectacular house on 3+ acres.

Exceptional waterfront estate located within the premier gated community of Oyster Harbors. This stunning five bedroom residence with lush landscaping and breathtaking views of West Bay and Nantucket Sound combine to create the ideal waterfront setting. The dramatic, light filled interior spaces have been thoughtfully designed and offer expansive windows with beautiful water views. Anchoring the home is a well-equipped kitchen with a spacious dining area opening into a great room with vaulted ceilings and fireplace. There's a handsome study/den and spacious and elegant first floor master bedroom. Custom columns, built-ins and beautiful wood floors enhance these spaces. Additional bedrooms on the 2nd level along with a private bedroom suite with sitting room, kitchen and bath are perfect for family gatherings or large scale entertaining. Amenities include an in-ground pool and private deep water dock. Included in this offering is a separate one acre building parcel.

Grand waterfront located in prestigious Oyster Harbors. Elaborate architectural details set the tone in this sprawling 17 room home with over 9,000 sq. ft. of living space featuring a chef's kitchen, formal dining room, living room with fireplace and first floor master suite with fireplace and sitting area. The stunning great room showcases the views of Cotuit Bay with expansive windows. Complete with in-ground pool, spa and private sandy beach. Information contained herein is believed to be accurate, but should be independently verified by prospective buyers.

Luxury living in the private gated community of Oyster Harbors! Exclusive and luxurious waterfront residence overlooking the beautiful waters of North Bay offers the finest in seaside living. This special property has been creatively expanded and features exceptional attention to detail. The 6,742 square foot home offers 7 bedrooms with 2 first floor master suites, a beautifully designed kitchen, comfortable family room and great room with floor to ceiling walls of windows to take advantage of the stunning views. The lower level is complete with a home theater, entertainment room and spacious office with custom built-ins. Panoramic water and golf course views, an in-ground pool with pool house and private and substantial deep water dock combine to create an ideal setting for large scale entertaining and peaceful family living. Information contained herein is believed to be accurate, but should be independently verified by prospective buyers.

Luxurious Waterfront Estate with southern exposure overlooking the soothing waters of West Bay. Enjoy the magnificent southern exposure as you watch the boats navigating to and from Nauticus, Crosby, and Oyster Harbors Yacht Clubs. The 5,700+ sf residence was designed by architect Tom Catalano (Boston) with the extensive interior craftsmanship custom finished by WoodMeister Master Builders (Boston, Nantucket, N.Y., and VT.) This captivating residence provides warm and inviting living areas for family and friends and features large impressive rooms with high ceilings, detailed custom millwork, a gourmet kitchen, 5-bedrooms, 3-full baths, 2-half baths, a home office, 2 fireplaces, a magnificent sun room overlooking the water, an expansive deck with multiple sitting areas, and a dingy dock on West Bay. All info. should be verified.

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Buyer Brokers of Cape Cod are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Buyer Brokers of Cape Cod shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated March 7, 2017. All properties are subject to prior sale, changes, or withdrawal.

Buyer Brokers of Cape Cod has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.

Testimonials

“It is certainly not a difficult task in referring Buyer Brokers of Cape Cod, McKenna Associates to anyone who is looking for a home here on the Cape. You are such a class act!”